Propargyl bromide → 3-Hydroxy-1-prop-2-ynyl-1H-benzo[4,5]furo[3,2-d]pyrimidine-2,4-dione

HRID 550740Notes

Reaction equation

HRID 550740 reaction equation
COC1C=C(OC)C=CC=1C[O:6][N:7]1[C:12](=[O:13])[C:11]2[O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10]=2[NH:9][C:8]1=[O:21].[CH2:28](Br)[C:29]#[CH:30]>C1(C)C=CC=CC=1>[OH:6][N:7]1[C:12](=[O:13])[C:11]2[O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10]=2[N:9]([CH2:30][C:29]#[CH:28])[C:8]1=[O:21]

Participants

4

Reactant 2

HCID 7842Propargyl bromideHCID 672018793-(2,4-Dimethoxy-benzyloxy)-1H-benzo[4,5]furo[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 117158243-Hydroxy-1-prop-2-ynyl-1H-benzo[4,5]furo[3,2-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following general procedure B2 and D1, 3-(2,4-dimethoxy-benzyloxy)-1H-benzo[4,5]furo[3,2-d]pyrimidine-2,4-dione was alkylated with an 80% solution of propargyl bromide in toluene and subsequently deprotected to provide the title compound as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 3.49 (t, J=2 Hz, 1H); 5.15 (d, J=2 Hz, 2H); 7.53 (dd, J=8 Hz, 1H); 7.70 (dd, J=8 Hz, 1H); 7.85 (d, J=8 Hz, 1H); 8.19 (d, J=8 Hz, 1H); Ret. time=1.86 min., m/z=257.0.

Sources & evidence

ORD record
ord-c23afdf01ebe40af9f4f9a9ec528cf69
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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